JP7719917B2 - Surfactants for agricultural products - Google Patents

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Patent Application No. 62/988,203, filed March 11, 2020, the entire contents of which are incorporated herein by reference.

The present disclosure relates to surfactants for use in agricultural products. Such surfactants may include derivatives of amino acids that have surface-active properties.

Surfactants (molecules with surface-active properties) are widely used in commercial agricultural formulations. These formulations may contain a variety of active agricultural agents, such as pesticides, plant growth regulators, fungicides, herbicides, and insecticides. Many such active agricultural agents may exhibit limited water solubility or be prone to crystallization. Precipitation of the active agricultural agent can result in a loss of efficacy. If the active agent becomes concentrated in the precipitate, uniform distribution is hindered upon application to the field. Therefore, surfactants may be included in the formulation to improve the solubility, wetting, and spreading of the active agent.

Surfactants can be nonionic, zwitterionic, cationic, or anionic. In principle, any surfactant class (e.g., cationic, anionic, nonionic, amphoteric) is suitable, but it is also possible that a formulation may contain a combination of two or more surfactants from two or more surfactant classes.

Surfactants are often amphiphilic molecules with a relatively water-insoluble hydrophobic "tail" group and a relatively water-soluble hydrophilic "head" group. These compounds can adsorb at interfaces, such as those between two liquids, between gas and liquid, or between solids and liquids. In systems containing a relatively polar component and a relatively nonpolar component, the hydrophobic tail preferentially interacts with the relatively nonpolar component, while the hydrophilic head preferentially interacts with the relatively polar component. In the case of an interface between water and oil, the hydrophilic head group preferentially extends into the water, while the hydrophobic tail preferentially extends into the oil. When added to an air-water interface, the hydrophilic head group preferentially extends into the water, while the hydrophobic tail preferentially extends into the gas. The presence of a surfactant disrupts at least some of the intermolecular interactions between water molecules, replacing them with generally weaker interactions between at least some of the water molecules and the surfactant. This results in a reduction in surface tension and may also act to stabilize the interface.

At sufficiently high concentrations, surfactants can form aggregates that act to limit the exposure of their hydrophobic tails to polar solvents. One such aggregate is a micelle. In a typical micelle, the molecules are arranged in a spherical fashion, with the surfactant's hydrophobic tail preferentially located on the inside of the sphere and the surfactant's hydrophilic head preferentially located on the outside of the micelle, where the head preferentially interacts with more polar solvents. The effect a given compound has on surface tension and the concentration at which it forms micelles can be useful characteristics for defining a surfactant.

The present disclosure provides formulations of agricultural products, such as pesticides, plant growth regulators, fungicides, herbicides, and insecticides. These products can be formulated to include one or more surfactants from one or more surfactant classes disclosed herein. The surfactants can be used as emulsifiers, wetting agents, dispersants, and/or agents to improve spreading. Additionally, surfactants can be used as adjuvants and agents to control spin drift.

The present disclosure provides surfactants for agricultural products in the form of amino acid derivatives that have surface-active properties. The amino acids may be natural or synthetic, or may be obtained via a ring-opening reaction of molecules such as lactams, e.g., caprolactam. The amino acids may be functionalized to form compounds with surface-active properties. Characteristically, these compounds may have a low critical micelle concentration (CMC) and/or the ability to reduce the surface tension of liquids.

The present disclosure provides a formulation for a pesticide or plant growth regulator, which comprises at least one surfactant of formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C _{The 6} alkyl includes a surfactant, which may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; a counterion, which may optionally be present and, if present, associated with the compound, which counterion is selected from the group consisting of chloride, bromide, iodide, and hydroxide; a pesticide or plant growth regulator; and a water-insoluble solvent.

The present disclosure further provides a formulation for a disinfectant, which comprises at least one surfactant of formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C _{The 6} alkyl optionally includes a surfactant, which may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; an optional counterion associated with the compound, which, if present, is selected from the group consisting of chloride, bromide, iodide, and hydroxide; an optional co-surfactant; and an optional carrier agent, such as a solvent or solid carrier.

The present disclosure further provides a formulation for a herbicide, which comprises at least one surfactant of formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C _{The 6} alkyl optionally may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; a counterion associated with the compound that may optionally be present and, if present, is selected from the group consisting of chloride, bromide, iodide, and hydroxide; one or more herbicides; a water-insoluble solvent; and water.

The present disclosure further provides a formulation for an insecticide, which comprises at least one surfactant of formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; and the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl is
a surfactant, optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; an optional counterion associated with the compound, when present, selected from the group consisting of chloride, bromide, iodide, and hydroxide; a biocide, an optional antifoaming agent, an optional antifreeze agent, and water.

The above and other features of the present disclosure, as well as the methods for achieving them, will become more apparent and better understood by referring to the following description of the embodiments in conjunction with the accompanying drawings.

FIG. 1 shows a plot of surface tension versus concentration measured at pH=7 for Surfactant 1, as described in Example 1b, where the Y-axis represents surface tension (γ) in units of milliNewtons per meter (mN/m) and the X-axis represents concentration (c) in units of millimolar (mM). FIG. 2 shows a plot of dynamic surface tension as a change in surface tension versus time for Surfactant 1, as described in Example 1c, where the Y-axis represents surface tension in milliNewtons per meter (mN/m) and the X-axis represents surface elapsed time in milliseconds (ms). FIG. 3 shows a plot of surface tension versus concentration measured at pH=7 for surfactant 2, as described in Example 2b, where the Y-axis represents surface tension (γ) in units of millinewtons per meter (mN/m) and the X-axis represents concentration (c) in units of millimolar (mM). FIG. 4 shows a plot of dynamic surface tension as a change in surface tension versus time for Surfactant 2, as described in Example 2c, where the Y-axis represents surface tension in milliNewtons per meter (mN/m) and the X-axis represents surface elapsed time in milliseconds (ms). FIG. 5 shows a plot of surface tension versus concentration measured for surfactant 3 at pH=7, as described in Example 3b, where the Y-axis represents surface tension (γ) in milliNewtons per meter (mN/m) and the X-axis represents concentration (c) in millimolar (mM). FIG. 6 shows a plot of dynamic surface tension as a change in surface tension versus time for Surfactant 3, as described in Example 3c, where the Y-axis represents surface tension in milliNewtons per meter (mN/m) and the X-axis represents surface elapsed time in milliseconds (ms). FIG. 7 shows a plot of surface tension versus concentration measured for surfactant 4 at pH=7, as described in Example 4b, where the Y-axis represents surface tension (γ) in milliNewtons per meter (mN/m) and the X-axis represents concentration (c) in millimolar (mM). FIG. 8 shows a plot of dynamic surface tension as a change in surface tension versus time for Surfactant 4, as described in Example 4c, where the Y-axis represents surface tension in milliNewtons per meter (mN/m) and the X-axis represents surface elapsed time in milliseconds (ms). FIG. 9 shows a plot of surface tension versus concentration measured for surfactant 5 at pH=7, as described in Example 5b, where the Y-axis represents surface tension (γ) in milliNewtons per meter (mN/m) and the X-axis represents concentration (c) in millimolar (mM). FIG. 10 shows a plot of dynamic surface tension as a change in surface tension versus time for Surfactant 5, as described in Example 5c, where the Y-axis represents surface tension in milliNewtons per meter (mN/m) and the X-axis represents surface elapsed time in milliseconds (ms).

As used herein, the phrase "within any range using these endpoints" literally means that any range may be selected from any two of the values listed before the phrase, regardless of whether the values are toward the low end of the list or toward the high end of the list. For example, a pair of values may be selected from the two lower values, the two higher values, or a lower value and an upper value.

As used herein, the term "alkyl" refers to any saturated carbon chain, which may be straight or branched.

As used herein, the phrase "surface active" means that the associated compound is capable of lowering the surface tension of the medium in which it is at least partially dissolved and/or the interfacial tension with other phases, and thus may be at least partially adsorbed to the air-liquid interface and/or other interfaces. The term "surfactant" may be applied to such compounds.

With respect to imprecision, the terms "about" and "approximately" may be used interchangeably and refer to a measurement that includes the stated measurement and any measurement that is reasonably close to the stated measurement. A measurement that is reasonably close to the stated measurement deviates from the stated measurement by a reasonably small amount that is understood and readily ascertained by one of ordinary skill in the relevant art. Such deviations may be attributed, for example, to measurement error or small adjustments made to optimize performance. If it is determined that the value for such a reasonably small difference would not be readily ascertained by one of ordinary skill in the relevant art, then the terms "about" and "approximately" may be understood to mean plus or minus 10% of the stated value.

The present disclosure provides formulations for agricultural products such as pesticides, plant growth regulators, fungicides, insecticides, and herbicides.

I. Pesticide and Plant Growth Regulator Formulations Active agricultural chemicals, such as pesticides, have traditionally been provided to end users in various concentrated forms that can be diluted by the end user with water or other suitable vehicles to form ready-to-use formulations. Such concentrated forms include solid formulations, e.g., dusts, and liquid formulations. In many applications, liquid formulations are preferred because they can avoid problems such as the splashing of toxic dusts and their slow dissolution in diluents.

Liquid concentrate formulations include so-called emulsion concentrates and soluble liquid concentrates. Emulsion concentrates contain a pesticide, a water-insoluble solvent, and an emulsifier, and when added to water, form, either naturally or after mixing, an oil-in-water emulsion in which the agricultural active ingredient is primarily present in the emulsion droplets. This type of concentrate formulation is particularly suitable for water-insoluble/poorly water-soluble agricultural active ingredients, where the recommended concentration in the ready-to-use formulation exceeds the solubility of the agricultural active ingredient.

The present disclosure provides pesticide or plant growth regulator formulations having high concentrations of agriculturally active agents that are suitable for long-term storage and delivery to end users who will ultimately treat plants by contacting the plants with agricultural formulations prepared from the concentrated pesticide formulations described herein.

The pesticide formulations of the present disclosure may include an agriculturally active agent (a pesticide or plant growth regulator), one or more surfactants or co-surfactants selected from one or more surfactant classes, and a water-insoluble solvent.

1. Pesticides The term "pesticide," as used herein, is known in the art and is described at least by the U.S. Environmental Protection Agency (EPA) in the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), the Pesticide and Environmental Pesticide Control Section (7 U.S.C. § 136(u)), the Code of Federal Regulations (CFR) regarding "Protection of the Environment," and EPA regulations at 40 U.S.C. § 152.3. A pesticide is typically recognized in the art as a substance used to prevent, destroy, repel, control, and/or mitigate any pest. A pest is an organism that is harmful to humans or the environment, but does not include any endoparasites of living humans or other living animals, or any fungi, bacteria, viruses, or other microorganisms that reside on or in living humans or other living animals. In other words, the term "pest" typically does not include any organism that causes infection or disease to humans or animals. Additionally, the term "pesticides," as used herein, typically does not include any human or animal drugs or medicines, any articles that are "novel animal drugs" as defined in the art, any liquid sterilants applied to devices used inside the human body, and/or any products intended for use against fungi, bacteria, viruses, or other microorganisms in or on living humans or other living animals. Furthermore, pesticides of the present disclosure typically do not include drugs or medicines used to control disease in humans or animals (such as livestock and pets).

As used herein, the term "plant growth regulator" means a compound that, through physiological action, accelerates or retards the rate of growth or maturation, or otherwise alters the behavior or products of ornamental plants or crops.

Pesticides and plant growth regulators particularly contemplated for use in the present invention are organic compounds, preferably synthetic organic compounds. Suitable pesticides and plant growth regulators include triazoles, strobilurins, alkylene bis(dithiocarbamate) compounds, benzimidazoles, phenoxycarboxylic acids, benzoic acids, ureas, sulfonylureas, triazines, pyridine carboxylic acids, neonicotinides, amidines, organophosphates, and pyrethroids. Pesticides may have a water solubility of 1 g/L or less.

In the concentrated formulations of the present disclosure, the pesticide or plant growth regulator may be present in an amount of about 5% by weight or more, about 10% by weight or more, about 15% by weight or more, about 20% by weight or more, or about 25% by weight or less, about 30% by weight or less, about 35% by weight or less, about 40% by weight or less, or within any range using these endpoints, based on the weight of the composition.

2. Surfactants The pesticide formulations of the present disclosure contain one or more surfactants, also referred to as a surfactant system. The surfactant system is included to emulsify the composition and/or act as an adjuvant. The surfactant system includes at least one surfactant, which may be an amphoteric surfactant, zwitterionic surfactant, cationic surfactant, or nonionic surfactant, and, optionally, at least one other surfactant, which may be an amphoteric surfactant, zwitterionic surfactant, cationic surfactant, nonionic surfactant, or a combination thereof. Such surfactants should be physically and chemically compatible with the essential ingredients described herein or should not otherwise unduly impair product stability, aesthetics, or performance.

Surfactants suitable for use in the pesticide formulations of the present disclosure are one or more surfactants and/or co-surfactants of Formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C _{The 6} alkyl includes surfactants and/or co-surfactants, which may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; and counterions associated with this compound, which may optionally be present and, if present, are selected from the group consisting of chloride, bromide, iodide, and hydroxide.

In particular, suitable surfactants or co-surfactants may include any one or more of surfactants 1 to 5 described herein.

The concentration of the surfactant system in the pesticide formulation may be in the range of about 20% by weight or more, about 30% by weight or more, about 40% by weight or more, or about 50% by weight or less, about 60% by weight or less, about 70% by weight or less, or about 80% by weight or less, or any range using any of these endpoints, based on the weight of the composition.

3. Water-Insoluble Solvents The pesticide formulations of the present disclosure may contain a water-insoluble solvent. A solvent is considered water-insoluble if its water solubility at 20° C. is about 10 g/1 L of water or less, about 5 g/1 L of water or less, about 1 g/1 L of water or less, or about 0.1 g/1 L of water or less.

Suitable water-insoluble solvents may include aromatic solvents such as those sold under the Solvesso trademark, and water-insoluble alcohols such as linear or branched, aliphatic or aromatic, saturated or unsaturated alcohols having at least 6 carbon atoms.

4. Other Additives The pesticide formulation may contain other additives such as additional surfactants, water, thickeners, deposition aids, drift retardants, salts, stabilizers, penetrants, spreading agents, wetting agents, builders, extenders, emulsifiers, dispersants, suspending agents, plant penetrants, translocators, oils, activators, foliar nutrients, compatibilizers, drift retardants, foam retardants, buffers, inverting agents, soil penetrants, stabilizers, UV filter substances, feeding stimulants, detergents, sinking agents, binders, liquid carriers, dry carriers such as attapulgite, kaolinite, vermiculite, starch polymers, corn cob, and combinations thereof. Pesticide formulations may also include additional chemical compounds that are not pesticides, such as activators, antifeedants, antifouling agents, attractants, sterilizers, disinfectants, fumigants, pheromones, repellents, defoliants, desiccants, insect growth regulators, plant growth regulators, synergists, adjuvants, and combinations thereof.

These additives may be present in the pesticide formulation, independently, in amounts of about 0% by weight or more, about 5% by weight or more, about 10% by weight or more, about 15% by weight or more, or about 20% by weight or less, about 25% by weight or less, about 30% by weight or less, or within any range using these endpoints.

Additional surfactants, such as additional anionic, nonionic, cationic, amphoteric, and zwitterionic surfactants, may be present in concentrated compositions at concentrations of about 5% by weight or more, about 10% by weight or more, about 15% by weight or more, about 20% by weight or more, or about 25% by weight or less, about 30% by weight or less, about 35% by weight or less, about 40% by weight or less, or any range using these endpoints, based on the weight of the composition.

Water may be present in a concentrated composition at a concentration of about 0% by weight or more, about 5% by weight or more, about 10% by weight or more, about 20% by weight or more, about 30% by weight or more, or about 35% by weight or less, about 45% by weight or less, about 55% by weight or less, about 65% by weight or less, or within any range using these endpoints, based on the weight of the composition.

Polymers may be included in the concentrate composition as thickeners, deposition promoters, or shatter inhibitors. Suitable polymers may include polysaccharide ethers and synthetic polymers.

Water-soluble organic solvents such as glycol ethers such as butyl diglycol, N-formyl-morpholine, short-chain fatty alcohols, and propylene carbonate may be present in the pesticide formulation in a weight ratio of up to 1:2 water-soluble organic solvent:water-insoluble organic solvent.

5. Method of Making The method includes combining the surfactant system, pesticide, and optionally a solvent. This step may also include adding any of the additives mentioned above. The components and compounds mentioned above may be added in any order and in any amount relative to one or more of each other, either all at once or in one or more separate steps, e.g., in portions.

6. Methods of Use The concentrated pesticide formulations of the present disclosure may be in the form of a liquid at room temperature and atmospheric pressure in which the agriculturally active ingredients are dissolved.

Concentrated pesticide formulations are intended to be mixed with an aqueous medium, typically tap water, before final use. The concentrated composition is added to the tank either before, simultaneously with, or after the aqueous medium (water) is added to the tank. The concentrated pesticide composition is thereby diluted to the appropriate concentration of agricultural active ingredient.

The water content in the diluted pesticide formulations of the present disclosure may be about 75% by weight or more, about 90% by weight or more, about 99% by weight or more, or about 99.9% by weight or more, based on the total weight of the diluted composition, and ultimately depends on the amount of water required to dilute the agricultural active ingredients in the concentrated pesticide formulations of the present disclosure to the desired concentration of the ready-to-use composition.

When mixed with an aqueous medium and diluted, the agriculturally active ingredient is uniformly distributed in the aqueous medium in the form of a solution or fine emulsion, and can be substantially diluted without any crystal growth occurring.

Plant treatment can be carried out by contacting the plant to be treated with diluted pesticide formulation that is ready to be used with any conventional method.As used herein, the term "plant" refers to the stem, leaf, and fruit of the plant that are visible above ground, as well as the root and even the seed.The amount of active ingredient that is contacted with plant is preferably sufficient for the active ingredient to exert its pesticidal activity or plant growth regulating activity, i.e., effective amount.

II. Fungicide Formulations The present disclosure provides fungicide formulations. The fungicide formulations may be in solid or liquid form. The fungi for which the formulations can be used include: Basidiomycetes, Ascomycetes, Adalomycetes, or Fungi Imperfecti, particularly heifers, oidia, eyespot, fusarioses, Fusarium roseum, and Fusarium nivale.
These harmful fungi include net blotch, leaf blotch, Septoria spot, and sin Rhizoctonia. These harmful fungi can cause disease on most vegetables and plants, but especially on cereals such as wheat, barley, rye, oats, or their hybrids, and on rice and corn.

The disinfectant formulation may include a disinfectant, an emulsifier component such as one or more surfactants or co-surfactants selected from one or more surfactant classes, an optional co-emulsifier, and an optional carrier agent such as a solvent or solid carrier.

1. Fungicide The fungicide formulation comprises a fungicide. Suitable fungicides include, but are not limited to, azoxystrobin, benalaxyl, carbendazim, chlorothalonil, kupfer, cymoxanil, cyproconazol, difenoconazole, dinocap, epoxiconazole, fluazinam, flusilazol, flutriafol, folpel, fosetyl aluminum, kresoxim methyl, hexaconazole, mancozeb, metalaxyl, metconazole, myclobutanil, ofurace, fentin hydroxide, prochloraz, pyrimethanil, soufre, tebucanazol, and tetraconazole, and mixtures thereof. Suitable herbicides include, but are not limited to, alachlor, aclonifen, acetochlor, amidosulfuron, aminotriazole, atrazine, bentazon, bifenox, bromoxyl octanoate, bromoxynil, clethodim, clodinafop-propargyl, chloridazon, chlorsulfuron, chlortoluron, clomazone, cycloxydim, desmedifan, dicamba, dicyclofop-methyl, diurea, diflufenicanil, dimithenamid, ethofumesate, fluazifop, fluazifop-p-butyl, fluorochloridone, fluroxypyr, glufosinate, glyphosate, galoxyfop-R, ioxynil octanoate, isoproturon, isoxaben, methyl Included are tamitron, metazachlor, metolachlor, metsulfuron-methyl, nicosulfuron, notoflurazone, oryzalin, oxadiazon, oxyfluorfen, paracat, pendimethalin, phenmedipham, phenoxyprop-p-ethyl, propaquizafop, prosulfocarb, quizalofop, sulcotrione, sulfosate, terbuthylazine, triasulfuron, triclopyr, triflualin, and triflusulfon-methyl, which may be used individually or in mixtures with one another.

The amount of disinfectant may be about 1% by weight or more, about 5% by weight or more, about 10% by weight or more, about 20% by weight or more, about 30% by weight or more, about 40% by weight or more, or about 50% by weight or less, about 60% by weight or less, about 70% by weight or less, about 80% by weight or less, about 90% by weight or less, or any combination of ranges using these endpoints, based on the total weight of the liquid disinfectant formulation.

2. Surfactants The fungicide formulations of the present invention contain one or more surfactants, also referred to as a surfactant system. The surfactant system may be used as a dispersing agent or wetting agent. The surfactant system may also be used as an emulsifier component to form a stable emulsion of the liquid fungicide formulation when prepared for agricultural use. The emulsifier component may also be used to form a stable emulsion concentrate. The surfactant system includes at least one surfactant, which may be an amphoteric surfactant, zwitterionic surfactant, cationic surfactant, or nonionic surfactant, and, optionally, at least one other surfactant, which may be an amphoteric surfactant, zwitterionic surfactant, cationic surfactant, nonionic surfactant, or a combination thereof.

Surfactants suitable for use in the disinfectant formulations of the present disclosure are one or more surfactants and/or co-surfactants of Formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C _{The 6} alkyl includes surfactants and/or co-surfactants, which may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; and counterions associated with this compound, which may optionally be present and, if present, are selected from the group consisting of chloride, bromide, iodide, and hydroxide.

In particular, suitable surfactants or co-surfactants may include any one or more of surfactants 1 to 5 described herein.

The total amount of one or more surfactants in the disinfectant formulation can be about 1% by weight or more, about 5% by weight or more, about 10% by weight or more, or about 15% by weight or less, about 20% by weight or less, about 25% by weight or less, about 30% by weight or less, about 35% by weight or less, or within any range using these endpoints.

3. Co-emulsifier or Co-surfactant The disinfectant composition may include an optional co-emulsifier or co-surfactant. The optional co-surfactant may be an anionic surfactant and/or a nonionic surfactant, and may include surfactants of the present disclosure as well as other surfactants. For example, anionic surfactants may include surfactants of the present disclosure or any surfactant known in the art, such as alkali, alkaline earth, or ammonium salts of fatty acids, such as potassium stearate; alkyl sulfates, alkyl ether sulfates, alkyl sulfonates or iso-alkyl sulfonates; alkyl naphthalene sulfonates; alkyl methyl ester sulfonates; acyl glutamates; alkyl sulfosuccinates; sarcosinates, such as sodium lauroyl sarcosinate; or taurates, and combinations thereof. The anionic surfactant may be present in the emulsifier component in any amount.

Nonionic emulsifiers may include surfactants of the present disclosure or any surfactant known in the art, such as alkoxylated animal or vegetable oils and fats such as corn oil ethoxylate, soybean oil ethoxylate, castor oil ethoxylate, and tallow fatty ethoxylates; glycerol esters such as glycerol monostearate; fatty alcohol alkoxylates and oxoalcohol alkoxylates; fatty acid alkoxylates such as oleic acid ethoxylate; alkylphenol alkoxylates such as isononylphenol ethoxylate; fatty amine alkoxylates; fatty acid amide alkoxylates; sugar surfactants such as sorbitan fatty acid esters (e.g., sorbitan monooleate and sorbitan tristearate); polyoxyethylene sorbitan fatty acid esters; alkyl polyglycosides; N-alkyl gluconamides; alkyl methyl sulfoxides; alkyl dimethyl phosphine oxides such as tetradecyl dimethyl phosphine oxide; and combinations thereof.

4. Carrier Agents The fungicide formulations of the present disclosure may contain a carrier agent. As used herein, the term "carrier" refers to a substance, natural or synthetic, organic or inorganic, that, when combined with an active ingredient, facilitates its application to plants, seeds, or soil. Thus, the carrier is usually inert, but at the same time, must be agriculturally acceptable, particularly for the plants to be treated. The carrier may be a solid (such as clay, natural or synthetic silicates, silicon dioxide, resins, waxes, or solid fertilizers) or a liquid (such as water, alcohol, ketone, petroleum fractions, aromatic or paraffinic hydrocarbons, chlorinated hydrocarbons, liquefied gases, etc.).

5. Other Additives Fungicide formulations may contain other additives such as stabilizers, penetrants, spreading agents, wetting agents, builders, extenders, emulsifiers, dispersants, suspending agents, plant penetrants, translocators, oils, activators, foliar nutrients, compatibilizers, anti-drift agents, anti-foam agents, buffers, phase inversion agents, soil penetrants, stabilizers, UV filter substances, feeding stimulants, detergents, sedimentation agents, binders, liquid carriers, dry carriers such as attapulgite, kaolinite, vermiculite, starch polymers, corncob, and combinations thereof. Pesticide formulations may also contain additional chemical compounds that are not pesticides, such as activators, anti-feeding substances, antifouling agents, attractants, sterilizers, disinfectants, fumigants, pheromones, repellents, defoliants, desiccants, insect growth regulators, plant growth regulators, synergists, adjuvants, and combinations thereof.

These additives may be present in the pesticide formulation, independently, in amounts of about 0% by weight or more, about 5% by weight or more, about 10% by weight or more, about 15% by weight or more, or about 20% by weight or less, about 25% by weight or less, about 30% by weight or less, or within any range using these endpoints.

6. Fungicide Emulsions Liquid fungicide formulations can be added to water or another solvent to form agricultural emulsions at the time of sale and/or use. Typically, a well-formed agricultural emulsion is milky white, blooms (i.e., forms) naturally, and has sufficient stability for effective application. However, fungicide emulsions of the present disclosure are not limited to such parameters and may have other characteristics indicative of good emulsion formation.

The present disclosure provides an aqueous fungicide formulation comprising the fungicide formulation described above and water. The liquid fungicide formulation may be combined with water in a spray tank or in a separate tank prior to addition to the spray tank. For example, the liquid fungicide formulation may be added to a separate container and/or spray tank that contains or is separate from the water. The term "diluted" indicates that the liquid agricultural fungicide formulation includes water.

The water in the diluted disinfectant formulation may be present in an amount of about 5% by weight or more, about 10% by weight or more, about 20% by weight or more, about 30% by weight or more, about 40% by weight or more, about 50% by weight or more, or about 60% by weight or less, about 70% by weight or less, about 80% by weight or less, about 90% by weight or less, about 99% by weight or less, about 99.5% by weight or less, or within any range using these endpoints, based on the diluted disinfectant formulation.

The disinfectant may be present in the diluted disinfectant formulation in an amount of about 0.00001% by weight or more, about 0.0001% by weight or more, about 0.001% by weight or more, about 0.01% by weight or more, about 0.1% by weight or more, about 1% by weight or more, or about 2% by weight or less, about 4% by weight or less, about 6% by weight or less, about 8% by weight or less, about 10% by weight or less, or within any range using these endpoints.

The fungicide may be present in an amount of about 100 g/hectare or more, about 200 g/hectare or more, about 300 g/hectare or more, about 400 g/hectare or more, about 500 g/hectare or more, or about 600 g/hectare or less, about 700 g/hectare or less, about 800 g/hectare or less, about 900 g/hectare or less, about 1000 g/hectare or less, or any range using these endpoints (or the equivalent thereof).

7. Emulsion Concentrates The present disclosure provides disinfectant emulsions that can be formed using emulsion concentrates (also known in the art as "EC"). The liquid disinfectant compositions described above may or may not be EC. Emulsion concentrates can be liquids having a viscosity at 25°C of about 1 cps or more, 20 cps or more, 40 cps or more, 60 cps or more, 80 cps or more, 100 cps or more, or 120 cps or less, 140 cps or less, 160 cps or less, 180 cps or less, 200 cps or less, or any range using these endpoints, up to 200 cps, 50-200 cps, 100-200 cps, or about 200 cps or less. Without intending to be bound by any particular theory, it is believed that a viscosity of about 200 cps or less at 25°C promotes bloom and efficient formation of the emulsion when an emulsifiable concentrate is used.

The emulsion concentrate itself may be anhydrous, i.e., contain no water. Alternatively, the emulsion concentrate may contain water. The emulsion concentrate may contain water in an amount of 5% by weight or less, 2.5% by weight or less, 1% by weight or less, 0.5% by weight or less, or 0.1% by weight or less. The emulsion concentrate may contain less than 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1 part by weight of water per 100 parts by weight of the emulsion concentrate. The emulsion concentrate is a single oil-like phase, e.g., a hydrophobic phase, that is free of water. As described in more detail below, when added to water or another solvent, the emulsion concentrate may bloom to form a milky white agricultural emulsion with little or no phase separation.

The emulsion concentrate may contain a single phase. In other words, the emulsion concentrate may not contain a distinct non-polar phase and a distinct polar phase, but instead may contain a single phase containing the active ingredient (fungicide), surfactant system, optional co-surfactant, and/or optional water-insoluble solvent. It should be understood that a single phase may contain partial phase separation, but typically does not contain complete phase separation. At low temperatures, phase separation may occur. The emulsion concentrate may be described as containing or being the surfactant system and fungicide described above (e.g., excluding the optional solvent and/or excluding the optional co-surfactant).

8. Solid Formulations By solid compositions, mention may be made of powders or dispersions suitable for dusting, in particular extruded, extruded or extruded particulate compositions. Solid formulations can be formed by impregnating the active agent into a carrier powder or by granulation of the powder.

The amount of active agent in these granule compositions can be about 1% by weight or more, 10% by weight or more, 20% by weight or more, 30% by weight or more, or about 40% by weight or less, about 50% by weight or less, about 60% by weight or less, about 70% by weight or less, about 80% by weight or less, or any range using these endpoints.

Wettable powder formulations (or spray dusts) may contain the active agent in an amount of about 20% by weight or more, about 30% by weight or more, about 40% by weight or more, or about 50% by weight or more, about 60% by weight or less, about 70% by weight or less, about 80% by weight or less, about 90% by weight or less, about 95% by weight or less, or any range using these endpoints.

Wettable powder formulations may contain a wetting agent, such as a surfactant, which may include a surfactant of the present disclosure, in an amount of about 0% by weight or more, about 1% by weight or more, about 2% by weight or more, or about 3% by weight or less, about 4% by weight or less, about 5% by weight or less, or within any range using these endpoints.

Wettable powder formulations may contain a dispersing agent, such as a surfactant, which may include a surfactant of the present disclosure, in an amount of about 3% by weight or more, about 4% by weight or more, about 5% by weight or more, about 6% by weight or more, or about 7% by weight or less, about 8% by weight or less, about 9% by weight or less, or about 10% by weight or less, or within any range using these endpoints.

Wettable powder formulations may contain a solid carrier, which may include any solid carrier known in the art, in an amount of about 0% by weight or more, about 1% by weight or more, about 2% by weight or more, about 3% by weight or more, about 4% by weight or more, about 5% by weight or more, or about 6% by weight or less, about 7% by weight or less, about 8% by weight or less, about 9% by weight or less, about 10% by weight or less, or any range using these endpoints.

Wettable powder formulations may contain one or more stabilizers and/or other additives such as pigments, colorants, penetrants, adhesion promoters, or anticaking agents.

To prepare these wettable powder formulations or spray powders, the active ingredient is intimately mixed with other ingredients in a suitable mixing device, and the resulting mixture is ground in a mill or other suitable grinding equipment. This results in wettable and suspendable spray powders. They can therefore be suspended in water at any concentration, making these suspensions particularly useful for seed treatment.

In addition to wettable powder formulations, pastes can also be prepared. The conditions and methods for preparing and using pastes, as well as their application, are the same as those for wettable powders or spray powders.

Dispersible granule compositions can be prepared by agglomeration in a suitable granulation system to provide a dust composition similar to a wettable powder formulation.

III. Herbicide Formulations The present disclosure further provides formulations of herbicides. These formulations may be applied to plants in a herbicidally effective amount to effectively control one or more plant species from one or more of the following genera, including, but not limited to, Abutilon, Amaranthus, Artemisia, Asclepias, Avena, Axonopus, Borrelia, Brachiaria, Brassica, Bromus, Chenopodium, Cirsium, Commelina, Convolvulus, Cynodon, Cyperus, Digitaria, Echinochloa, Eleusine, Erymus, and the like. Elymus, Equisetum, Erodium, Helianthus, Imperata, Ipomoea, Kochia, Lolium, Malva, Oryza, Ottochloa, Panicum, Paspalum, Phalaris aris, Phragmites, Polygonum, Portulaca, Pteridium, Pueraria, Rubus, Salsola, Setaria, Sida, Sinapis, Sorghum, Triticum, Typha
), Ulex, Xanthium, and Zea.

The herbicide formulations of the present disclosure may include a herbicide, an optional second herbicide, one or more surfactants selected from one or more surfactant classes, a water-insoluble solvent, and water.

1. Herbicide The herbicide formulations of the present disclosure may include a herbicide or a water-soluble salt thereof. Suitable herbicides may include 2,4-D (2,4-dichlorophenoxyacetic acid), 2,4-DB (4-(2,4-dichlorophenoxy)butyric acid), aminocyclopyrachlor, aminopyralid, clopyralid, dicamba, glyphosate, MCPA, MCPB, picloram, triclopyr, or mixtures thereof.

Water-soluble salts of herbicides can include salts containing one or more cations selected from the class of organic ammonium cations, which can have from 1 to about 12 carbon atoms. Examples of organic ammonium cations include isopropylammonium, diglycolammonium (2-(2-aminoethoxy)ethanolammonium), dimethylammonium, diethylammonium, triethylammonium, monoethanolammonium, dimethylethanolammonium, diethanolammonium, triethanolammonium, triisopropanolammonium, tetramethylammonium, tetraethylammonium, N,N,N-trimethylethanolammonium (choline), and N,N-bis-(3-aminopropyl)methylammonium (BAPMA).

In addition, water-soluble salts of herbicides may include salts containing one or more cations selected from inorganic cations such as sodium and/or potassium.

For acidic herbicides, such as auxin-type herbicides, the herbicide may be present in the herbicide formulation at a concentration of about 100 grams acid equivalent per liter (g ae/L) or more, about 200 g ae/L or more, about 300 g ae/L or more, or about 400 g ae/L or less, about 500 g ae/L or less, about 600 g ae/L or less, or about 700 g ae/L or less, or about 800 g ae/L or less, or about 900 g ae/L or less, or about 1 ...200 g ae/L or less, or about 1300 g ae/L or less, or about 1400 g ae/L or less, or about 1500 g ae/L or less, or about
The soluble solids may be present in an amount of about 1000 g ae/L or less, about 625 g ae/L or less, about 625 g ae/L or less, or within any range using these endpoints.

Some herbicidal active ingredients described herein do not contain acid-type functional groups, and for these active ingredients, the terms "acid equivalent" and "acid equivalent basis" do not accurately describe the amount of second herbicide present. Generally, in such cases, the terms "active ingredient" or "active ingredient basis" may be used to describe the amount of second herbicide active ingredient present. If the active ingredient does not have an acid equivalent, for example, grams active ingredient per liter (g ai/L) may be used instead of gram acid equivalent per liter (g ae/L), or grams active ingredient per kilogram (g ai/kg) may be used instead of gram acid equivalent per kilogram (g ae/kg).

2. Optionally present second herbicide Suitable second herbicides include, but are not limited to, esters of 4-CPA, 4-CPB, 4-CPP, 2,4-D, 3,4-DA, 2,4-DB, 3,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DP, 2,4,5-T, 2,4,5-TB, and 2,3,6-TBA, allidochlor, acetochlor, acifluorfen, aclonifen, alachlor, alloxydim, arorac, ametridione, ametryn, amivudine, amicarbazone, amidosulfuron, aminocyclopyrachlor esters, aminopyralid esters, amiprophos-methyl, amitrole, anilofos, anisrone, asulam, atraton, atrazine, azafenidine, azimsulfuron, aziprothrin, burban, BCPC, and beflubutamid. , benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron, bensulide, bentazon, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bicylopyrone, bifenox, biranaphos, bispyribac, bromacil, bromobonyl, bromobutide, bromofenoxime, bromoxynil, brompyrazone, butachlor, butafenacil, butamifos, butenachlor, butidazole, buthiuron, butralin, butroxydim, buturon, butyrate, cafenstrole, cafendichlor, carbaslam, carbetamide, carboxazole Chlorprocarb, carfentrazone, CDEA, CEPC, chlormethoxyfen, chloramben, chloranocryl, chlorradifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid esters, chloransulam, CPMF, CPPC, cledazine, cumyluron, cyanatrin , cyanazine, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyperquat, cyprazine, cyprazole, cypromide, dymron, dalapon, dazomet, delaclor, desmedipham, desmetrin, diallate, dicamba ester, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop, diclosulam , Diethamquat, Diethathyl, Diphenopentene, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Dimefron, Dimepiperate, Dimethachlor, Dimethamethrin, Dimethenamid, Dimethenamid-P, Dimexano, Dimidazone, Dinitramine, Dinitramine, Dinophenate, Dinoprop, Dinosam, Dinoseb, Dinoterb, Difenamide, Dipropetrin, Dikuwa t, disul, dithiopyr, diuron, DMPA, DNOC, EBEP, eglinadin, endosal, epronaz, epronaz, EPTC, ervon, esprocarb, ethalfluralin, ethametsulfuron, ethidimuron, ethiolate, ethofumesate, ethoxyfen, ethoxysulfuron, ethinofen, etonipromide, etonipromide, etobenzanide, EXD, phenas Ram, fenasulam, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P, fenoxasulfone, fenteracol, fentiaprop, fentrazamide, fenuron, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufena Set, Flufenican, Flufenpyr, Flumetsulam, Flumezin, Flumiclorac, Flumioxazin, Flumipropin, Fluometuron, Fluorodifen, Fluoroglycofen, Fluoromidine, Fluoronitrofen, Fluothiuron, Flupoxam, Flupoxam, Flupropacil, Flupropanate, Flupyrsulfuron, Fluridone, Flurochloridone, Non-liquid fluroxypyr ester, Fluroxypyr-meptyl, Flurtamone, Fluthiacet, Fomesafen, Foramsulfuron, Fosamine, Furyloxyfen, Glyphosate, Halauxfen, Halauxfen-methyl, Halosafen, Halosulfuron, Haloxydine, Haloxyfop, Haloxyfop-P, Hexazinone , Imazamethabenz, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Indanofan, Indaziflam, Iodobonyl, Iodosulfuron, Ioxinil, Ipazine, Ipfencarbazone, Iprimidam, Isocarbamide, Isosyl, Isomethiozine, Isonoruron, Isoporinate, Isoproparin, Isoproturon, Isouron, Isoxaben, I Soxaclortol, isoxaflutole, isoxapirifop, carbutilate, ketospiradox, lactofen, lenacil, linuron, MCPA ester, MCPA-thioethyl, MCPA-EHE, MCPB ester, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamifop, Metamitron, metazachlor, metazosulfuron, metofluran, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, metoprothrin, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metoslam, metoxuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monolinuron, monuron, morphamcort, naproanilide, napropamide, naptalam, nebulon, nicosulfuron, nipiraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, norlon, OCH, orbencarb, orthosulfamuron, oryzalin, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclofen Mefon, oxyfluorfen, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidon, petoxamide, phenisofam, phenmedipham, phenmedipham-ethyl, fenobenzuron, picloram ester, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, procyazin, prodiamine, profliazole, profluralin, profoxydim, proglinadin, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfarin, prosulfocarb, prosulfuron, proxan, prinachlor, pidanone, pyrachlor Nil, pyraflufen, pyrasulfotole, pyrazolinate, pyrazosulfuron, pyrazoxifen, pyribenzoxim, pyributicarb, pyrichlor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, pyrosulfotole, pyroxasulfone, piroxsulam, quinclorac, quinmerac, quinoclamine, quinonamide, quizalofop, quizalofop-P, rodetanil, rimsulfuron, saflufenacil, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simetryn, sulcotrione, sulfurate, sulfentrazone, sulfometuron, sulfosulfuron, sulglicapin, swep, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor
The active ingredient may be selected from terbumetone, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, non-liquid triclopyr ester, thidiazimine, thidiazuron, thidiazuron, thiencarbazone-methyl, thifensulfuron, thiobencarb, thiocarbazil, thioclorim, topramezone, tralkoxydim, triallate, triasulfuron, triaziflam, tribenuron, tricamba, tridiphan, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, triphop, trifopsim, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vernolate, xylachlor, and mixtures and derivatives thereof.

The second herbicide, when used, may be present at a concentration of about 0 g ae/L or more, 0.1 g ae/L or more, 10 g ae/L or more, 50 g ae/L or more, 100 g ae/L or more, or 200 g ae/L or more.
The soluble solids are present in an amount of about 1000 g ae/L or less, about 300 g ae/L or less, about 400 g ae/L or less, or within any range using these endpoints.

Some second herbicide active agents described herein do not contain acid-type functional groups, and for these active ingredients, the terms "acid equivalent" and "acid equivalent basis" do not accurately describe the amount of second herbicide present. Generally, in such cases, the terms "active ingredient" or "active ingredient basis" may be used to describe the amount of second herbicide active ingredient present. If the active ingredient does not have an acid equivalent, for example, grams active ingredient per liter (g ai/L) may be used instead of gram acid equivalent per liter (g ae/L), or grams active ingredient per kilogram (g ai/kg) may be used instead of gram acid equivalent per kilogram (g ae/kg).

3. Surfactants Surfactants suitable for use in the herbicide formulations of the present disclosure are one or more surfactants and/or co-surfactants of Formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C _{The 6} alkyl includes surfactants and/or co-surfactants, which may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; and counterions associated with this compound, which may optionally be present and, if present, are selected from the group consisting of chloride, bromide, iodide, and hydroxide.

In particular, suitable surfactants or co-surfactants may include any one or more of Surfactants 1-5 described herein.

The herbicide formulation may contain one or more surfactants in an amount of about 0% by weight or more, about 2% by weight or more, about 4% by weight or more, about 6% by weight or more, about 8% by weight or more, or about 10% by weight or less, about 12% by weight or less, about 14% by weight or less, about 16% by weight or less, or within any range using these endpoints.

4. Water-Insoluble Solvents Suitable water-insoluble, immiscible organic solvents include those derived or produced from natural non-petroleum sources, such as plants and animals, including vegetable oils, seed oils, animal oils, and the like, such as N,N-dimethylcaprylamide (N,N-dimethyloctanamide), N,N-dimethylcapramide (N,N-dimethyldecanamide), and mixtures thereof, which are available from BASF Corp. (Florham Park, N.J.) as Agnique® AMD 810 and Agnique® AMD 10; Clariant (Charlotte, N.C.) as Genegen® 4166, Genegen® 4231, and Genegen® 4296; Stepan (Northfield, Ill.) as Hallcomid M-8-10 and Hallcomid M-10; and AkzoNobel (Chicago, Ill.) as Amid DM10 and DM810. Further examples of naturally occurring organic solvents include morpholine amides of caprylic/capric fatty acids (C ₈ /C ₁₀ ), commercially available as JEFFSOL® AG-1730 Solvent from Huntsman International LLC (The Woodlands, Tex.).

Other suitable water-insoluble solvents include aromatic hydrocarbons, mixed naphthalene and alkyl naphthalene fractions, aromatic solvents, especially alkyl-substituted benzenes such as xylene or propyl benzene fractions; C 1 -C 6 esters of fatty acids derived from vegetable, seed, or animal oils, such as methyl caproate, methyl caprylate, methyl caprate, methyl laurate, methyl myristate, methyl palmitate, methyl stearate, methyl oleate, methyl linoleate, methyl _linolenate ; ketones such as isophorone and trimethylcyclohexanone (dihydroisophorone ₎ ; acetates such as methyl, ethyl, propyl, butyl, pentyl, hexyl, or heptyl acetate; and the like, as described by Huntsman (The Journal of Examples of suitable water-immiscible organic solvents include cyclic alkyl carbonates such as propylene carbonate and butylene carbonate, commercially available as JEFFSOL® alkylene carbonates from JEFFSOL® Alkylene Carbonate, available from Huntsman, Woodlands, Tex., dibutyl carbonate, also from Huntsman, and mixtures of any of the water-immiscible organic solvents described herein.

The water-insoluble solvent may be present in the herbicide formulation in an amount of about 0% by weight or more, about 10% by weight or more, about 20% by weight or more, or about 30% by weight or less, about 40% by weight or less, about 50% by weight or less, or within any range using these endpoints.

5. Water Water may be present in the herbicide formulations of the present disclosure to act as both an aqueous solvent and a carrier for the ingredients in the described compositions.

The herbicide formulations of the present disclosure may contain water in an amount of about 200 g/L or more, about 300 g/L or more, about 400 g/L or more, or about 500 g/L or less, about 600 g/L or less, about 700 g/L or less, about 800 g/L or less, or within any range using these endpoints.

The herbicide formulation may contain one or more compatible additional ingredients. These additional ingredients may include, for example, one or more pesticides or other ingredients that may be dissolved or dispersed in the composition and may be selected from acaricides, algicides, feeding deterrents, bird killers, fungicides, bird repellents, sterilizers, defoliants, desiccants, disinfectants, bactericides, herbicide safeners, herbicides, insect attractants, insecticides, insect repellents, mammal repellents, mating disruptants, snailicides, nematicides, plant activators, plant growth regulators, rodenticides, semiochemicals, synergists, and virucides. Any other additional ingredients that provide functional benefits, such as, for example, antifoaming agents, antimicrobial agents, buffers, corrosion inhibitors, dispersants, dyes, fragrances, freezing point depressants, neutralizing agents, odorants, penetration aids, sequestering agents, overspray suppressants, spreading agents, stabilizers, tackifiers, viscosity modifying additives, water soluble solvents, etc., may also be included in these compositions.

When the described herbicide formulations are used in combination with additional active ingredients, such as herbicide active ingredients, the compositions described herein can be formulated with the other active ingredient(s) as a premix concentrate, or can be mixed with water in a tank with the other active ingredient(s) for spray application, or can be applied sequentially with the other active ingredient(s) by separate spray applications.

7. Method of Making The herbicide formulations of the present disclosure may be made by the following steps: 1) preparing a solution of one or more second herbicides and a surfactant in an organic solvent; 2) adding the solution prepared in step 1) to a concentrated aqueous solution of a water-soluble salt of the herbicide with thorough mixing to form a clear solution; and 3) adding any compatible additional active or inactive ingredients, as desired.

Alternatively, the herbicide formulations of the present disclosure may be prepared by the following steps: 1) providing a liquid second herbicide and optionally mixing it with an organic solvent and a surfactant; 2) adding the composition prepared in step 1) to a concentrated aqueous solution of a water-soluble salt of the herbicide with sufficient mixing to form a clear solution; and 3) optionally adding any compatible additional active or inactive ingredients.

Suitable water-compatible ingredients that may be added to the herbicide formulation include, but are not limited to, water-soluble or water-insoluble dispersible surfactants, such as the surfactants of the present disclosure, water-insoluble active ingredients, and, if desired, other inert ingredients, such as pH buffers, wetting agents, antifreeze agents, antifoaming agents, and biocides.

8. Method of Use The aqueous herbicide formulations described herein can be diluted, if desired, into aqueous spray mixtures intended for agricultural applications, such as for weed control in fields or turf. Such herbicide formulations are typically diluted with an inert carrier, such as water, before application. For example, diluted herbicide formulations, which are typically applied to weeds, the locus where weeds are growing, or the locus where weeds may eventually emerge, can contain an amount of agriculturally active agent (herbicide) of about 0.0001% by weight or more, about 0.001% by weight or more, about 0.01% by weight or more, about 0.1% by weight or more, about 1% by weight or more, or about 2% by weight or less, about 3% by weight or less, about 4% by weight or less, or about 5% by weight or less, or within any range using these endpoints. The herbicide formulations of the present disclosure can be applied to weeds or their locus, for example, by using conventional ground or aerial sprayers, by addition to irrigation water, and by other conventional means known to those skilled in the art.

The herbicide formulations of the present disclosure may be used in controlling undesirable vegetation in crops having single, multiple, or stacked genetic traits that confer tolerance to one or more herbicide chemicals and/or inhibitors having single or multiple modes of action.

IV. Pesticide Formulations The present disclosure also provides formulations of pesticides. Such formulations may be in liquid or solid form, such as emulsifiable concentrates, oil-in-water (O/W) emulsions, suspension concentrates, and wettable powders.

The pesticide formulation may include a pesticide, one or more surfactants selected from one or more surfactant classes, an optional defoamer, an optional antifreeze, and water.

1. Insecticides Suitable insecticides may include one or more pyrethroids, such as synthetic pyrethroids; organophosphate compounds, such as chlorpyrifos-ethyl, chlorpyrifos-methyl, pirimiphos-methyl, fenitrothion, and the like; phenyl ethers, such as pyriproxyfen; benzoyl ureas, such as flufenoxuron; carbamates, such as fenoxycarb, carbosulfan, and the like; nicotinoids, such as acetamiprid; pyridine carboxamides, such as flonicamid, and the like. The pyrethroid may be selected from one or more of bifenthrin, zeta-cypermethrin, alpha-cypermethrin, tetra-methrin, lambda-cyhalothrin, fenvalerate, cyfluthrin, bio-resmethrin, permethrin, delta-methrin.

The insecticide may be present in the insecticide formulation in an amount, measured by weight per volume, of about 1% or more, about 5% or more, about 10% or more, or about 15% or less, about 20% or less, or within any range using these endpoints.

2. Surfactants The pesticide formulation may include one or more surfactants selected from one or more surfactant classes, collectively referred to as a surfactant system.

Surfactants suitable for use in the insecticide formulations of the present disclosure are one or more surfactants and/or co-surfactants of Formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C _{The 6} alkyl includes surfactants and/or co-surfactants, which may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; and counterions associated with this compound, which may optionally be present and, if present, are selected from the group consisting of chloride, bromide, iodide, and hydroxide.

In particular, suitable surfactants or co-surfactants may include any one or more of surfactants 1 to 5 described herein.

The surfactant system may be present in the pesticide formulation in an amount, measured by weight per volume, of about 1% or more, about 5% or more, about 10% or more, about 15% or more, or about 20% or less, about 25% or less, about 30% or less, about 35% or less, about 40% or less, or within any range using these endpoints.

3. Optional Antifoaming Agents Optional antifoaming agents in the pesticide formulation may include silicone emulsions and/or surfactants such as those of the present disclosure.

The antifoaming agent may be present in the insecticide formulation in an amount, measured by weight per volume, of about 0.0% or more, about 0.1% or more, about 0.2% or more, about 0.3% or more, about 0.4% or more, about 0.5% or more, or about 0.6% or less, about 0.7% or less, about 0.8% or less, about 0.9% or less, about 1.0% or less, or within any range using these endpoints.

4. Optional Antifreeze Agents The pesticide formulation may include an optional antifreeze agent. Suitable antifreeze agents may include diols, such as alkyl diols or dialkyl diols.

The insecticide formulation may contain an antifreeze agent in an amount, measured by weight per volume, of about 0% or more, about 1% or more, about 2% or more, about 3% or more, about 4% or more, about 5% or more, or about 6% or less, about 7% or less, about 8% or less, about 9% or less, about 10% or less, or within any range using these endpoints.

5. Water The pesticide formulations may contain water in an amount, measured by weight per volume, of about 25% or more, about 30% or more, about 35% or more, about 40% or more, about 45% or more, about 50% or more, about 55% or more, or about 60% or less, about 65% or less, about 70% or less, about 75% or less, about 80% or less, about 85% or less, about 90% or less, about 95% or less, about 98% or less, or within any range using these endpoints.

6. Other Additives The pesticide formulations of the present disclosure may include viscosity modifiers, such as thickeners such as cellulose derivatives, polyacrylamides, polyvinyl alcohols, polyvinylpyrrolidones, and natural gums.

The viscosity modifier may be present in the pesticide formulation in any amount suitable to modify the viscosity to the desired level.

The insecticide formulations of the present disclosure may also include a preservative. Suitable preservatives include methylparaben.

Preservatives may be present in the pesticide formulation in an amount, measured by weight per volume, of greater than or equal to 0.0%, greater than or equal to 0.1%, or less than or equal to 0.2%, or within any range using these endpoints.

V. Adjuvants In addition to the uses described above, the surfactants of the present disclosure can also be used as adjuvants in the formulation of agricultural active agents such as pesticides, plant growth regulators, herbicides, fungicides, and insecticides. The adjuvant compounds can be used to improve one or more properties of the formulation of agricultural active agents, such as storage stability, ease of handling, and effectiveness in controlling target organisms.

VI. Spray drift reduction agent Spray drift refers to the unintentional dispersion of pesticides and other agricultural active agents, including off-target contamination. This can lead to human health hazards, environmental pollution, and land damage. The surfactants of the present disclosure can be used to reduce the amount of driftable fine particles of agricultural active agent formulations in both aerial and ground spray applications.

The surfactants and mixtures thereof of the present disclosure can be incorporated into aqueous spray mixtures, for example, by direct tank mixing, with diluted formulations of agriculturally active agents such as pesticides, plant growth regulators, fungicides, herbicides, or insecticides.

The optimal spray droplet size depends on the application for which the composition is being used. Droplets that are too large will result in reduced spray coverage; for example, large droplets will land in certain areas, while intervening areas will receive little or no spray coverage. The maximum acceptable droplet size may depend on the amount of composition applied per unit area and the required uniformity of the spray coverage. Smaller droplets provide more uniform coverage but are more prone to drift during spraying. Therefore, application parameters such as the uniformity of the spray coverage must be balanced against the tendency of smaller droplets to drift. For example, if it is particularly windy during spraying, larger droplets may be required to reduce drift, while smaller droplets may be acceptable on calmer days. In addition to the physical properties of a particular aqueous composition, spray droplet size may also depend on the spray equipment, e.g., nozzle size and configuration.

The reduction in spray overspray can be attributed to a variety of factors, including a reduction in the production of fine spray droplets (smallest diameter <150 μm) and an increase in the volume median diameter (VMD) of the spray droplets. In either case, for any given spray device, application, and conditions, and based on the surfactant used, the median diameter of multiple spray droplets produced using the surfactants described herein will be increased over the surfactant-free spray compositions of the present disclosure.

VII. Surfactants The present disclosure provides surfactants for use in agricultural products in the form of derivatives of amino acids. The amino acids may be natural or synthetic, or may be obtained from the ring-opening reaction of lactams such as caprolactam. The compounds of the present disclosure have been shown to have surface-active properties and can be used, for example, as surfactants and wetting agents. In particular, the present disclosure provides compounds of formula I:

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; and a counterion associated with the compound that may optionally be present and, if present, is selected from the group consisting of chloride, bromide, iodide, and hydroxide.

One specific compound provided by the present disclosure is 6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexane-1-aminium iodide (Surfactant 1), which has the following formula:

A second specific compound provided by the present disclosure is dodecyl 6-(dimethylamino)hexanoate N-oxide (Surfactant 2), which has the following formula:

In the above structure, the "N→O" notation is intended to refer to a non-ionic bonding interaction between nitrogen and oxygen.

A third specific compound provided by the present disclosure is 6-(dodecyloxy)-N,N-dimethyl-6-oxohexane-1-aminium chloride (Surfactant 3), which has the following formula:

A fourth specific compound provided by the present disclosure is 4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate (surfactant 4
) and has the formula:

A fifth specific compound provided by the present disclosure is 6-(dodecyloxy)-6-oxohexane-1-aminium chloride (Surfactant 5), which has the following formula:

These surfactants can be synthesized by a variety of methods. One such method involves ring-opening a lactam to obtain an amino acid with an N-terminus and a C-terminus. The N-terminus can be reacted with one or more alkylating agents and/or acids to obtain a quaternary ammonium salt. Alternatively, the N-terminus can be reacted with an oxidizing agent to obtain an amine N-oxide. The C-terminus can be reacted with an alcohol in the presence of an acid to obtain an ester.

The amino acid may be natural or synthetic, or may be derived from the ring-opening reaction of a lactam, such as caprolactam. The ring-opening reaction may be acid- or alkali-catalyzed; an example of an acid-catalyzed reaction is shown in Scheme 1 below.

An amino acid can have as few as one carbon or as many as 12 carbons between the N-terminus and C-terminus. The alkyl chain can be branched or straight. The alkyl chain can be interrupted by nitrogen, oxygen, or sulfur. The alkyl chain can be further substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carboxyl, and carboxylate. The N-terminal nitrogen can be acylated or alkylated with one or more alkyl groups. For example, the amino acid can be 6-(dimethylamino)hexanoic acid.

Surfactant 1 can be synthesized as shown in Scheme 2 below. As shown, 6-aminohexanoic acid is treated with formaldehyde in formic acid under reflux to give 6-(dimethylamino)hexanoic acid. The free carboxylic acid is then treated with an alcohol such as dodecanol in the presence of p-toluenesulfonic acid (PTSA) in toluene to give the corresponding ester, dodecyl 6-(dimethylamino)hexanoate. The N-terminus is then alkylated with methyl iodide in the presence of sodium carbonate.

Surfactant 2 can be synthesized as shown in Scheme 3 below. As shown, 6-aminohexanoic acid is treated with formaldehyde in formic acid under reflux to yield 6-(dimethylamino)hexanoic acid. The free carboxylic acid is then treated with an alcohol such as dodecanol in the presence of p-toluenesulfonic acid (PTSA) in toluene to yield the corresponding ester, dodecyl 6-(dimethylamino)hexanoate. The N-terminus is then oxidized with hydrogen peroxide to yield the amine oxide.

Surfactant 3 can be synthesized as shown in Scheme 4 below. As shown, 6-aminohexanoic acid is treated with formaldehyde in formic acid under reflux to give 6-(dimethylamino)hexanoic acid. The free carboxylic acid is then treated with an alcohol such as dodecanol in the presence of p-toluenesulfonic acid (PTSA) in toluene to give the corresponding ester, dodecyl 6-(dimethylamino)hexanoate. The N-terminus is then alkylated with methyl iodide in the presence of sodium carbonate.

Surfactant 4 can be synthesized as shown in Scheme 5 below. As shown, 6-aminohexanoic acid is treated with formaldehyde in formic acid at reflux to yield 6-(dimethylamino)hexanoic acid. The free carboxylic acid is then treated with an alcohol such as dodecanol in the presence of p-toluenesulfonic acid (PTSA) in toluene to yield the corresponding ester, dodecyl 6-(dimethylamino)hexanoate. The N-terminus is then treated with 1,4-butanesultone in ethyl acetate at reflux to yield the desired sulfonate.

Surfactant 5 can be synthesized as shown in Scheme 6 below. As shown, 6-aminohexanoic acid is treated with an alcohol in the presence of p-toluenesulfonic acid (PTSA) in toluene to give the corresponding ester, dodecyl 6-aminohexanoate. The N-terminus is protonated with hydrochloric acid to give the desired hydrochloride salt.

The compounds of the present disclosure exhibit surface-active properties. These properties can be measured and expressed in a variety of ways. One way surfactants can be expressed is by the molecule's critical micelle concentration (CMC). The CMC can be defined as the concentration of surfactant that forms micelles, above which all additional surfactant is incorporated into the micelles.

As surfactant concentration increases, surface tension decreases. When the surface is completely covered with surfactant molecules, micelles begin to form. This point represents the CMC, and thus the minimum surface tension. Adding more surfactant does not further affect the surface tension. The CMC can therefore be measured by observing the change in surface tension as a function of surfactant concentration. One such method for measuring this value is the Wilhelmy plate method. A Wilhelmy plate is typically a thin iridium-platinum plate attached to a balance by a wire and positioned perpendicular to the air-liquid interface. The balance is used to measure the force exerted on the plate due to wetting. This value is then used to calculate the surface tension (γ) according to Equation 1:
Formula 1: γ=F/l cosθ
where l is equal to the wetted perimeter (2w+2d, where w and d are the thickness and width of the plate, respectively), and for cos θ, the contact angle between the liquid and the plate is assumed to be 0 in the absence of an existing literature value.

Another parameter used to evaluate surfactant performance is dynamic surface tension. Dynamic surface tension is the value of surface tension over time for a particular surface or interface. For liquids to which surfactants have been added, this may differ from the equilibrium value. Immediately after the surface is created, the surface tension is equal to that of the pure liquid. As noted above, surfactants reduce surface tension, so the surface tension decreases until it reaches an equilibrium value. The time required to reach equilibrium depends on the diffusion and adsorption rates of the surfactant.

One method for measuring dynamic surface tension is with a maximum bubble pressure tensiometer. This device measures the maximum internal pressure of a bubble formed in a liquid by a capillary. The measured value corresponds to the surface tension at a specific surface time, which is the time from the start of bubble formation to the maximum pressure. The dependence of surface tension on surface time can be measured by varying the rate at which the bubbles are generated.

Surface-active compounds can also be evaluated by their ability to wet on solid substrates, as measured by contact angle. When a liquid droplet contacts a solid surface in a third medium, such as air, a three-phase line is formed between the liquid, the gas, and the solid. The angle between the surface and the unit vector of surface tension, which is tangent to the droplet and plays a role in the three-phase line, is expressed as the contact angle. The contact angle (also known as the wetting angle) is a measure of the wettability of a solid by a liquid. In the case of complete wetting, the liquid spreads completely over the solid, and the contact angle is 0°. Wetting properties are typically measured at concentrations between 1 and 100 x CMC for a given compound; however, since it is not a concentration-dependent property, measurements of wetting properties may be taken at higher or lower concentrations.

In one method, an optical contact angle goniometer can be used to measure contact angles. This instrument uses a digital camera and software to determine the contact angle by analyzing the contour shape of a sedentary drop of liquid on a surface.

Possible uses for the surface-active compounds of the present disclosure include formulations for use as shampoos, hair conditioners, detergents, spot-free rinse solutions, floor and carpet cleaners, cleaning agents for graffiti removal, wetting agents for crop protection, adjuvants for crop protection, and wetting agents for aerosol spray coatings.

Those skilled in the art will appreciate that small differences between compounds can lead to significantly different surfactant properties, and therefore different compounds may be used with different substrates in different applications.

The following non-limiting examples are provided to illustrate the different properties of different surfactants. Table 1 below associates surfactant abbreviations with their corresponding chemical structures.

Each of the five compounds is effective as a surfactant and is useful as a wetting or foaming agent, dispersant, emulsifier, and detergent, among other uses.

Surfactants 1, 3, and 5 are cationic. These surfactants are useful in both the applications mentioned above and in several additional specialty applications, such as surface treatments, personal hair care products, and can also be used to create water-repellent surfaces.

Surfactant 4 is nonionic and can be used in shampoos, detergents, hard surface cleaners, and a variety of other surface cleaning formulations.

Surfactant 5 is zwitterionic. These surfactants are useful as co-surfactants in all of the applications mentioned above.

Examples Nuclear magnetic resonance (NMR) spectroscopy was performed on a Bruker 500 MHz spectrometer. Critical micelle concentration (CMC) was determined by the Wilhelmy plate method using a tensiometer (DCAT 11, DataPhysics Instruments GmbH) equipped with a Pt-Ir plate.
The dynamic surface tension was determined at 23°C using a maximum bubble pressure tensiometer (Krüss BP100, Krüss GmbH). The contact angle was determined using an optical contact angle goniometer (OCA 15 Pro, DataPhysics GmbH) equipped with a digital camera.

Example 1a:
Synthesis of 6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide (Surfactant 1). 6-(Dimethylamino)hexanoic acid (11.99 g, 75.36 mmol) was dissolved in toluene (50 mL) in a round-bottom flask equipped with a Dean-Stark trap. Dodecanol (12.68 g, 75.36 mmol) and p-toluenesulfonic acid monohydrate (PTSA) (14.33 g, 75.36 mmol) were then added. The reaction was heated to reflux for 24 hours until no water was observed in the Dean-Stark trap. The solvent was removed under vacuum, and the resulting solid was washed with hexane. The solid was dissolved in dichloromethane (200 mL) and washed with saturated sodium carbonate to give dodecyl 6-(dimethylamino)hexanoate in 51% yield. 1H NMR (DMSO) δ 4.00 (t, J = 6.5 Hz, 2H), 2.27 (t, J = 7.3 Hz, 2H), 2.13-2.16 (m, 2H), 2.01 (s, 6H), 1.54-1.53 (m, 6H), 1.27-1.18 (m, 20H), 0.86 (t, 3H).

Dodecyl 6-(dimethylamino)hexanoate (1.0 g, 3.05 mmol) was dissolved in acetonitrile (10 mL). Sodium carbonate (0.388 g, 3.66 mmol) was then added, and the reaction was stirred at room temperature for 10 minutes. Methyl iodide (0.57 mL, 9.16 mmol) was added, and the reaction mixture was heated to 40° C. for 24 hours, then cooled to room temperature. The mixture was filtered and concentrated to give 6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide as a yellow solid in 92% yield. ^1H NMR (DMSO) δ 4.00 (t, J = 6.7Hz, 2H), 3.30-3.22 (m, 2H), 3.04 (s, 9H), 2.34 (t, J = 7.4Hz, 2H), 1 .70-1.63 (m, 2H), 1.62-1.46 (m, 4H), 1.31-1.20 (m, 20H), 0.86 (t, J=6.9Hz, 3H).

Example 1b:
Determining the Critical Micelle Concentration (CMC) of Surfactant 1 The critical micelle concentration (CMC) was determined. From the variation of surface tension with concentration in water, the CMC was determined to be approximately 1 mmol. The plateau value of the minimum surface tension achievable with this surfactant is approximately 33 mN/m, i.e., 33 mN/m ± 3.3 mN/m. Figure 1 is a plot of these results, showing surface tension versus concentration. From the plot, the surface tension is approximately 34 mN/m at the CMC and approximately 33.8 mN/m at concentrations of 1.0 mmol and above.

Example 1c:
Determination of Dynamic Surface Tension of Surfactant 1. Dynamic surface tension was determined with a maximum bubble pressure tensiometer, which measures the change in surface tension over time at a newly created air-water interface. Figure 2 presents a plot of the results as surface tension versus time, showing that in the time interval from 1 ms to 75 ms, the surface tension rapidly decreases from about 55.5 mN/m to about 39.9 mN/m. In the time interval from 75 ms to 50,410 ms, the surface tension decreases more slowly from about 39.9 mN/m to about 34 mN/m, asymptotically approaching the saturation value of surface tension at the CMC.

Example 1d:
Identification of Wetting Properties of Surfactant 1 In addition to surface tension and surface kinetics, the wetting properties of the compound were tested on various surfaces. For example, hydrophobic substrates such as polyethylene-HD exhibit surface wetting with a contact angle of 32°. On oleophobic and hydrophobic substrates such as Teflon, the measured contact angle was 67.1°, much lower than that of water (Table 2).

Example 2a:
Synthesis of Dodecyl 6-(dimethylamino)hexanoate N-Oxide (Surfactant 2) 6-(Dimethylamino)hexanoic acid (11.99 g, 75.36 mmol) was dissolved in toluene (50 mL) in a round-bottom flask equipped with a Dean-Stark trap. Next, dodecanol (12.68 g, 75.36 mmol) and p-toluenesulfonic acid monohydrate (PTSA) (14.33 g, 75.36 mmol) were added. The reaction was heated to reflux for 24 hours until no water was observed in the Dean-Stark trap. The solvent was removed under vacuum, and the resulting solid was washed with hexane. The solid was dissolved in dichloromethane (200 mL) and washed with saturated sodium carbonate to give dodecyl 6-(dimethylamino)hexanoate in 51% yield. ^1H NMR (DMSO) δ 4.00 (t, J = 6.5 Hz, 2H), 2.27 (t, J = 7.3 Hz, 2H), 2.13-2.16 (m, 2H), 2.01 (s, 6H), 1.54-1.53 (m, 6H), 1.27-1.18 (m, 20H), 0.86 (t, 3H).

Dodecyl 6-(dimethylamino)hexanoate (1.0 g, 3.05 mmol) was dissolved in distilled water (80 mL). Hydrogen peroxide (50% solution, 1.04 g, 30.5 mmol) was added. The reaction was heated to reflux for 12 hours, and then the solvent was removed in vacuo. The resulting solid was washed with acetone to give the desired N-oxide in 90% yield. ^1H NMR (500MHz, DMSO) δ 4.00 (t, J=6.6Hz, 2H), 3.30-3.26 (m, 2H), 3.18 (s, 6H), 2.31 (t, J=7.4Hz, 2H), 1 .76-1.73 (m, 2H), 1.54-1.57 (m, 4H), 1.30-1.24 (m, 22H), 0.86 (t, J=6.9Hz, 3H).

Example 2b:
Determining the Critical Micelle Concentration (CMC) of Surfactant 2 The critical micelle concentration (CMC) was determined. From the change in surface tension with concentration in water, the CMC was determined to be approximately 0.08 mmol. The plateau value of the minimum surface tension achievable with this surfactant is approximately 28 mN/m, i.e., 28 mN/m ± 2.8 mN/m. Figure 3 is a plot of these results, showing surface tension versus concentration. The resulting plot shows that the surface tension at the CMC is approximately 30 mN/m or less. The plot further shows that at concentrations of 0.08 mmol or greater, the surface tension is 30 mN/m or less.

Example 2c:
Dynamic Surface Tension Determination of Surfactant 2 Dynamic surface tension was determined using a maximum bubble pressure tensiometer, which measures the change in surface tension of a newly created air-water interface over time. Figure 4 shows a plot of surface tension versus time, showing that the compound fully saturated the surface in approximately 7.6 seconds. As can be seen from the plot, the dynamic surface tension is below 40 mN/m for surface dwell times of over 4900 ms.

Example 2d:
Identification of Wetting Properties of Surfactant 2 In addition to surface tension and surface kinetics, the wetting properties of the compound were tested on various surfaces. For example, hydrophobic substrates such as polyethylene-HD exhibit surface wetting with a contact angle of 39.3°, which is much lower than water. On oleophobic and hydrophobic substrates such as Teflon, the measured contact angle was 57.4°, which is much lower than water (Table 3).

Example 3a:
Synthesis of 6-(dodecyloxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride (Surfactant 3). 6-(Dimethylamino)hexanoic acid (11.99 g, 75.36 mmol) was dissolved in toluene (50 mL) in a round-bottom flask equipped with a Dean-Stark trap. Dodecanol (12.68 g, 75.36 mmol) and p-toluenesulfonic acid monohydrate (PTSA) (14.33 g, 75.36 mmol) were then added. The reaction was heated to reflux for 24 hours until no water was observed in the Dean-Stark trap. The solvent was removed under vacuum, and the resulting solid was washed with hexane. The solid was dissolved in dichloromethane (200 mL) and washed with saturated sodium carbonate to give dodecyl 6-(dimethylamino)hexanoate in 51% yield. ^1H NMR (DMSO) δ 4.00 (t, J = 6.5 Hz, 2H), 2.27 (t, J = 7.3 Hz, 2H), 2.13-2.16 (m, 2H), 2.01 (s, 6H), 1.54-1.53 (m, 6H), 1.27-1.18 (m, 20H), 0.86 (t, 3H).

Dodecyl 6-(dimethylamino)hexanoate (100 mg, 0.305 mmol) was dissolved in water (10 mL). Concentrated hydrochloric acid (11.14 mg, 0.305 mmol) was added.

Example 3b:
Determining the Critical Micelle Concentration (CMC) of Surfactant 3 The critical micelle concentration (CMC) was determined. From the change in surface tension with concentration in water, the CMC was determined to be approximately 1.4 mmol. The plateau value of the minimum surface tension achievable with this surfactant is approximately 30 mN/m, i.e., 30 mN/m ± 3 mN/m. Figure 5 is a plot of these results, showing surface tension versus concentration. The resulting plot shows that the surface tension at the CMC is approximately 30 mN/m or less. The plot further shows that at concentrations of 2.7 mmol or greater, the surface tension is 33 mN/m or less.

Example 3c:
Dynamic surface tension determination for surfactant 3. Dynamic surface tension was determined using a maximum bubble pressure tensiometer, which measures the change in surface tension of a newly created air-water interface over time. Figure 6 shows a plot of surface tension versus time, showing that over the time interval from 1 to 100 ms, the surface tension rapidly decreases from about 50 mN/m to about 40 mN/m. Over the time interval from 100 to 50,000 ms, the surface tension decreases slowly from 40 mN/m to about 34 mN/m, asymptotically approaching the saturation value of surface tension at the CMC.

Example 3d:
Identification of Wetting Properties of Surfactant 3 In addition to surface tension and surface kinetics, the wetting properties of the compound were tested on various surfaces. For example, hydrophobic substrates such as polyethylene-HD exhibit surface wetting with a contact angle of 42.5°. On oleophobic and hydrophobic substrates such as Teflon, the measured contact angle was 66.6°, much lower than that of water (Table 4).

Example 4a:
Synthesis of 4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate (Surfactant 4) 6-(Dimethylamino)hexanoic acid (11.99 g, 75.36 mmol) was dissolved in toluene (50 mL) in a round-bottom flask equipped with a Dean-Stark trap. Dodecanol (12.68 g, 75.36 mmol) and p-toluenesulfonic acid monohydrate (PTSA) (14.33 g, 75.36 mmol) were then added. The reaction was heated to reflux for 24 hours until no water was observed in the Dean-Stark trap. The solvent was removed in vacuo and the resulting solid was washed with hexane. The solid was dissolved in dichloromethane (200 mL) and washed with saturated sodium carbonate to give dodecyl 6-(dimethylamino)hexanoate in 51% yield. 1H NMR (DMSO) δ 4.00 (t, J = 6.5 Hz, 2H), 2.27 (t, J = 7.3 Hz, 2H), 2.13-2.16 (m, 2H), 2.01 (s, 6H), 1.54-1.53 (m, 6H), 1.27-1.18 (m, 20H), 0.86 (t, 3H).

Dodecyl 6-(dimethylamino)hexanoate (1.0 g, 3.05 mmol) was dissolved in ethyl acetate (30 mL). 1,4-butanesultone (0.62 g, 4.57 mmol) was then added, and the mixture was heated to reflux for 12 hours. The reaction was cooled to room temperature, and the solvent was removed in vacuo. 1H NMR (DMSO) δ 4.00 (t, J = 6.7 Hz, 2H), 3.29-3.15 (m, 4H), 2.97 (s, 6H), 2.47 (t, J = 7.4 Hz, 2H), 2.33 (t, J = 7.4 Hz, 2H), 1.81-1.70 (m, 2H), 1.66-1.55 (m, 6H), 1.32-1.23 (m, 20H).
, 0.86 (t, J=6.9Hz, 3H).

Example 4b:
Determining the Critical Micelle Concentration (CMC) of Surfactant 4 The critical micelle concentration (CMC) was determined. From the change in surface tension with concentration in water, the CMC was determined to be approximately 0.1 mmol. The plateau value of the minimum surface tension achievable with this surfactant is approximately 38 mN/m, i.e., 38 mN/m ± 3.8 mN/m. Figure 7 is a plot of these results, showing surface tension versus concentration. The resulting plot shows that the surface tension is approximately 38 mN/m at the CMC, and at concentrations of 1 mmol and above, the surface tension is 37 mN/m or less.

Example 4c:
Dynamic surface tension determination of Surfactant 4: Dynamic surface tension was determined using a maximum bubble pressure tensiometer, which measures the change in surface tension of a newly created air-water interface over time. Figure 8 shows a plot of surface tension versus time, indicating that the compound fully saturated the surface in approximately 1 second. From the plot, the dynamic surface tension is 40.5 mN/m or less for surface dwell times of 4000 ms or more.

Example 4d:
Identification of Wetting Properties of Surfactant 4 In addition to surface tension and surface kinetics, the wetting properties of the compound were tested on various surfaces. For example, hydrophobic substrates such as polyethylene-HD exhibit surface wetting with a contact angle of 46.5°. On oleophobic and hydrophobic substrates such as Teflon, the measured contact angle was 62.7°, much lower than that of water (Table 5).

Example 5a:
Synthesis of 6-(dodecyloxy)-6-oxohexano-1-aminium chloride (surfactant 5). 6-Aminohexanoic acid (5.0 g, 38.11 mmol) was dissolved in toluene (50 mL) in a round-bottom flask equipped with a Dean-Stark trap. Dodecanol (6.41 g, 38.11 mmol) and p-toluenesulfonic acid monohydrate (PTSA) (7.24 g, 38.11 mmol) were then added. The reaction was heated to reflux for 24 hours until no water was observed in the Dean-Stark trap. The solvent was removed under vacuum, and the resulting solid was washed with hexane. The solid was dissolved in dichloromethane (200 mL) and washed with saturated sodium carbonate to give dodecyl 6-aminohexanoate in 40% yield.

Dodecyl 6-aminohexanoate (100 mg, 0.363 mmol) was dissolved in water (10 mL), and then concentrated hydrochloric acid (13.23 mg, 0.363 mmol) was added.

Example 5b:
Determining the Critical Micelle Concentration (CMC) of Surfactant 5 The critical micelle concentration (CMC) was determined. From the change in surface tension with concentration in water, the CMC was determined to be approximately 0.75 mmol. The plateau value of the minimum surface tension achievable with this surfactant is approximately 23 mN/m, i.e., 23 mN/m ± 2.3 mN/m. Figure 9 is a plot of these results, showing surface tension versus concentration. The resulting plot shows that the surface tension is approximately 23 mN/m at the CMC, and at concentrations of 0.7 mmol and above, the surface tension is 23.2 mN/m or less.

Example 5c:
Dynamic surface tension determination of Surfactant 5: Dynamic surface tension was determined using a maximum bubble pressure tensiometer, which measures the change in surface tension of a newly created air-water interface over time. Figure 10 shows a plot of surface tension versus time, indicating that the compound fully saturated the surface in approximately 1.5 seconds. From the plot, the dynamic surface tension is 28.5 mN/m or less for surface dwell times of 3185 ms or more.

Example 5d:
Identification of Wetting Properties of Surfactant 5 In addition to surface tension and surface kinetics, the wetting properties of the compound were tested on various surfaces. For example, hydrophobic substrates such as polyethylene-HD exhibit a very low surface wetting with a contact angle of 16.6°. On oleophobic and hydrophobic substrates such as Teflon, the measured contact angle was 39.3°, much lower than that of water (Table 6).

Example 6:
Pesticide Formulations In this example, a concentrated formulation for use as a pesticide is provided, comprising a surfactant, which may be one or more of Surfactants 1-5 described herein. The ingredients of the formulation are shown below in Table 7. The formulation may also include additional surfactants, water, thickeners, deposition aids, drift retardants, and salts.

Example 7:
Formulations for Liquid Sanitizer Compositions In this example, a formulation for use as a liquid sanitizer composition is provided, comprising a surfactant, which may be one or more of Surfactants 1-5 described herein. The formulation is shown in Table 8 below.

Example 8:
Herbicide Formulations In this example, a formulation for use as a herbicide is provided that includes a surfactant, which may be one or more of Surfactants 1-5 described herein. The formulation is shown in Table 9 below.

Example 9:
Insecticide Formulations In this example, a formulation for use as an insecticide is provided, comprising a surfactant, which may be one or more of Surfactants 1-5 described herein. The formulation is shown in Table 10 below.

Aspect 1 is a formulation for an agrochemical, which comprises at least one surfactant of formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C _{The 6} alkyl includes a surfactant, which may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; a counterion associated with the compound, which may optionally be present and, if present, is selected from the group consisting of chloride, bromide, iodide, and hydroxide; and a pesticide.

Aspect 2 is the formulation described in Aspect 1, further comprising a water-insoluble solvent.

Aspect 3 is a surfactant represented by the following formula:

A formulation according to aspect 1 or aspect 2, wherein the compound is 6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexane-1-aminium iodide.

Aspect 4 is a surfactant represented by the following formula:

A formulation according to aspect 1 or aspect 2, wherein the compound is dodecyl 6-(dimethylamino)hexanoate N-oxide.

Aspect 5 is a surfactant represented by the following formula:

A formulation according to aspect 1 or aspect 2, wherein the compound is 6-(dodecyloxy)-N,N-dimethyl-6-oxohexane-1-aminium chloride.

Aspect 6 is a surfactant represented by the following formula:

A formulation according to aspect 1 or aspect 2, wherein the compound is 4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate.

Aspect 7 is a surfactant represented by the following formula:

A formulation according to aspect 1 or aspect 2, wherein the compound is 6-(dodecyloxy)-6-oxohexane-1-aminium chloride.

Aspect 8 is a formulation for a fungicide, which is represented by formula I:

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C wherein _{the 6} alkyl is optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; a counterion associated with the compound that is optionally present and, if present, is selected from the group consisting of chloride, bromide, iodide, and hydroxide; and a fungicide.

Aspect 9 is the formulation described in aspect 8, further comprising a co-surfactant.

Aspect 10 is the formulation of Aspect 8 or Aspect 9, further comprising a carrier agent.

Aspect 11 is a surfactant represented by the following formula:

A formulation according to any one of aspects 8 to 10, wherein the compound is 6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexane-1-aminium iodide.

Aspect 12 is a surfactant represented by the following formula:

A formulation according to any one of aspects 8 to 10, wherein the compound is dodecyl 6-(dimethylamino)hexanoate N-oxide.

Aspect 13 is a surfactant represented by the following formula:

A formulation according to any one of aspects 8 to 10, wherein the compound is 6-(dodecyloxy)-N,N-dimethyl-6-oxohexane-1-aminium chloride.

Aspect 14 is a surfactant represented by the following formula:

A formulation according to any one of aspects 8 to 10, wherein the compound is 4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate.

Aspect 15 is a surfactant represented by the following formula:

A formulation according to any one of aspects 8 to 10, wherein the compound is 6-(dodecyloxy)-6-oxohexane-1-aminium chloride.

Aspect 16 is a formulation for a herbicide, which comprises at least one surfactant of formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; and the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl is
a surfactant, which may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; a counterion, which may optionally be present and, if present, associated with the compound, which counterion is selected from the group consisting of chloride, bromide, iodide, and hydroxide; and a herbicide.

Aspect 17 is the formulation described in Aspect 16, further comprising a second herbicide.

Aspect 18 is the formulation described in Aspect 16 or Aspect 17, further comprising a water-insoluble solvent.

Aspect 19 is a formulation according to any one of aspects 16 to 18, further comprising water.

Aspect 20 is a surfactant represented by the following formula:

A formulation according to any one of aspects 16 to 19, wherein the compound is 6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexane-1-aminium iodide.

Aspect 21 is a surfactant represented by the following formula:

A formulation according to any one of aspects 16 to 19, wherein the compound is dodecyl 6-(dimethylamino)hexanoate N-oxide.

Aspect 22 is a surfactant represented by the following formula:

A formulation according to any one of aspects 16 to 19, wherein the compound is 6-(dodecyloxy)-N,N-dimethyl-6-oxohexane-1-aminium chloride.

Aspect 23 is a surfactant represented by the following formula:

A formulation according to any one of aspects 16 to 19, wherein the compound is 4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate.

Aspect 24 is a surfactant represented by the following formula:

A formulation according to any one of aspects 16 to 19, wherein the compound is 6-(dodecyloxy)-6-oxohexane-1-aminium chloride.

Aspect 25 is a formulation for an insecticide, which comprises at least one surfactant of formula I,

wherein R ¹ and R ² may be the same or different and may be selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl, where C ₁ -C ₆ alkyl may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; n is an integer from 2 to 5, inclusive; m is an integer from 9 to 20, inclusive; the terminal nitrogen may be further substituted with R ³ , where R ³ is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C ₁ -C ₆ alkyl, where C ₁ -C _{The 6} alkyl includes a surfactant, which may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; a counterion associated with the compound, which may optionally be present and, if present, is selected from the group consisting of chloride, bromide, iodide, and hydroxide; and a pesticide.

Aspect 26 is the formulation described in Aspect 25, further comprising an antifoaming agent.

Aspect 27 is the formulation of aspect 25 or aspect 26, further comprising a cryoprotectant.

Aspect 28 is the formulation of any one of aspects 25 to 27, further comprising water.

Aspect 29 is a surfactant represented by the following formula:

A formulation according to any one of aspects 25 to 27, wherein the compound is 6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexane-1-aminium iodide.

Aspect 30 is a surfactant represented by the following formula:

A formulation according to any one of aspects 25 to 27, wherein the compound is dodecyl 6-(dimethylamino)hexanoate N-oxide.

Aspect 31 is a surfactant represented by the following formula:

A formulation according to any one of aspects 25 to 27, wherein the compound is 6-(dodecyloxy)-N,N-dimethyl-6-oxohexane-1-aminium chloride.

Aspect 32 is a surfactant represented by the following formula:

A formulation according to any one of aspects 25 to 27, wherein the compound is 4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate.

Aspect 33 is a surfactant represented by the following formula:

A formulation according to any one of aspects 25 to 27, wherein the compound is 6-(dodecyloxy)-6-oxohexane-1-aminium chloride.

Aspect 34 is the formulation of Aspect 1 or Aspect 2, wherein the pesticide is an insecticide.

Aspect 35 is the formulation described in Aspect 34, further comprising an antifoaming agent.

Aspect 36 is the formulation of Aspect 34 or Aspect 35, further comprising a cryoprotectant.

Aspect 37 is a formulation according to any one of aspects 34 to 36, further comprising water.

Aspect 38 is a surfactant represented by the following formula:

6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexane-1-aminium iodide having the formula:
The following formula:

dodecyl 6-(dimethylamino)hexanoate N-oxide having the formula:
The following formula:

6-(dodecyloxy)-N,N-dimethyl-6-oxohexane-1-aminium chloride having the formula:
The following formula:

4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate having the formula
The following formula:

The formulation described in any one of Aspects 1, 2, or 34-37 includes at least one of: 6-(dodecyloxy)-6-oxohexane-1-aminium chloride having the formula:

Aspect 39 is a surfactant represented by the following formula:

6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexane-1-aminium iodide having the formula:
The following formula:

dodecyl 6-(dimethylamino)hexanoate N-oxide having the formula:
The following formula:

6-(dodecyloxy)-N,N-dimethyl-6-oxohexane-1-aminium chloride having the formula:
The following formula:

4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate having the formula
The following formula:

A formulation according to any one of aspects 8 to 10, comprising at least one of: 6-(dodecyloxy)-6-oxohexane-1-aminium chloride having the formula:

Aspect 40 is a surfactant represented by the following formula:

6-(dodecyloxy)-N,N,N-trimethyl-6-oxohexane-1-aminium iodide having the formula:
The following formula:

dodecyl 6-(dimethylamino)hexanoate N-oxide having the formula:
The following formula:

6-(dodecyloxy)-N,N-dimethyl-6-oxohexane-1-aminium chloride having the formula:
The following formula:

4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate having the formula
The following formula:

The formulation described in any one of aspects 16 to 19 includes at least one of: 6-(dodecyloxy)-6-oxohexane-1-aminium chloride having the formula:

Claims (13)

1. A formulation for a pesticide, comprising:
at least one surfactant and a pesticide;
Including,
The surfactant has the following formula:
Dodecyl 6-(dimethylamino)hexanoate N-oxide having the formula:
The following formula:
4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate having the formula
and combinations thereof,
formulation. The formulation of claim 1, further comprising a water-insoluble solvent. The formulation described in claim 1 or claim 2, wherein the pesticide is an insecticide. The formulation of claim 3, further comprising an antifoaming agent. The formulation of claim 3 or claim 4, further comprising a cryoprotectant. The formulation described in any one of claims 3 to 5, further comprising water. A formulation for a fungicide, comprising:
at least one surfactant and a disinfectant;
Including,
The surfactant has the following formula:
Dodecyl 6-(dimethylamino)hexanoate N-oxide having the formula:
The following formula:
4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate having the formula
and combinations thereof,
formulation. The formulation of claim 7, further comprising a co-surfactant. The formulation of claim 7 or claim 8, further comprising a carrier agent. 1. A formulation for a herbicide comprising:
at least one surfactant and a herbicide;
Including,
The surfactant has the following formula:
Dodecyl 6-(dimethylamino)hexanoate N-oxide having the formula:
The following formula:
4-((6-(dodecyloxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate having the formula
and combinations thereof,
formulation. The formulation of claim 10, further comprising a second herbicide. The formulation described in claim 10 or claim 11, further comprising a water-insoluble solvent. The formulation according to any one of claims 10 to 12, further comprising water.